Reality Check: Why I Left My Dream Job to Teach Online

This past Spring, I finished my third year of my dream job. I taught at a top-5 ranking elementary school in my state. My administration loved me and gave me creative license to teach how I thought worked best. I was the popular, young, male teacher that all the kids wanted to have. And many of the parents wanted their kids to be in my class because of the nontraditional approach that I brought to learning. Life was definitely good. Then, on the last day of the school year, while my students were still in the room, I decided to leave it all.

Out of curiosity, about one week before, I had checked the vacant job postings on my district’s web page and noticed that a position had opened at our public online academy. And I applied.

The interview went well, and I felt positive about being offered the job. But I kept it all a secret from my principal, my colleagues, and my students because I knew that saying goodbye would be heart-wrenching, and I was somehow hoping that I could still have my cake and eat it too.

Eventually, however, I realized that there were only crumbs left, and I had to explain where the cake went. That was when my classroom phone rang on the last day of the school year with the online school’s principal and a job offer on the other end.

I accepted the transfer and let the cat out of the bag to my original school family, packed up my things that day, and walked out of a traditional school building for what could be the last time, trading in face-time with students and the security of a classroom for an office and a laptop.

It really wasn’t until going to San Antonio a few weeks later for ISTE13 that I realized what I had really gotten myself into. With 20,000 tech-savvy educators gathered in one place, upon introducing myself to those whom I met I found myself answering the exact same question, “You’re an online middle school teacher, how does that work?” While I wanted to respond with a short, “I dunno” I found myself, instead, spouting off vague generalizations laced with educational buzzwords that served the purpose of making me sound somewhat legit. While that made me uncomfortable in the moment, it forced me to face the reality of having committed to participating in a completely new style of teaching and learning, one where the instructor must come down from his or her ivory tower of being the dispensary of information and knowledge, and take his or her new seat alongside the ranks of more self-directed learners.

So, if I didn’t realize what I was getting myself into, why did I decide to make the transition? Why leave the comforts of a 5-star school where I had built a positive reputation as a very identifiable face in the community to teach at a school with a much lower ranking and where some of my students won’t actually ever see my face at all?

I did it because I believe in the power of online technology. Yes, it is an effective tool in the classroom when used by teachers who are strong at what they already do. But it goes well beyond that. I went online because I believe in the power of online technology to, not only enhance the learning process, but to change lives, and to do so in a rich, meaningful, and lasting way.

See, my life story is on the Internet. In college, I paid for rent by launching a somewhat successful music career on Myspace. It was when I really started to network on Facebook that I met my future wife. While I completed my student teaching, she started a lifestyle blog has now become her full-time job, enabling her to supplement our income enough to be a stay-at-home mom. And over the past year, I went from hallway conversations with colleagues down the hall to collaborating with educators who live around the world, and connecting with them so deeply that my best friends now don’t live in my neighborhood. They live in Oregon, Texas, Wisconsin, Georgia, New Hampshire, and into parts of Canada.

Online technology isn’t just a train passing in the night, it’s a bus that just crashed into the middle of your living room. It is the biggest social revolution since the invention of the telephone. And it is a force so powerful that it has shrunken a world of 7 billion people small enough to carry around with you in your pocket.

Working my dream job for the past three years was fantastic. But it was really only that, a dream. Now, reality has set in, and it requires a Wi-Fi hotspot.


Dave Guymon

Dave Guymon is a public online middle school teacher, edtech blogger, and the author of If You Can’t Fail, It Doesn’t Count.

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Audrey McLaren

Hi Dave, I made the exact same decision for pretty much the same reasons 5 years go, and it was the absolute best decision of my life. My job and my life rock. Welcome to online! I teach 100% synchronously online, and I blog about it a lot. If there's anything you need help with, I'm there. Online means a lot of different things, and you'll find some things are different, but bottom line, if you cared about your kids when you were f2f, you'll continue to in this new environment.

Summer Len Diamond

What an awesome testimony to leap of faith in learning! Definitely an inspiration to use your passion and gifts for the learning of others. Thanks for your post. Loved it.


Best wishes for happiness and success in your new position! I think your students will feel your charisma. I look forward to reading more about your journey. Thanks for sharing! Cheers!

Madalyn M

Hi Mr. Guymon, I don't know if you will ever read this but I want you to know that all the Rimrock kids miss and think about you often. Your way of teaching really changed the way I think of things. Our raps and skits helped me remember things I needed to know on tests now. We all miss you!

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